Family-friendly vacation rentals in Olean

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Olean

  • Total vacation rentals

    Explore 20 vacation rentals in Olean

  • Nightly prices starting at

    Olean vacation rentals start at ﺩ.ﺇ 294 per night before taxes and fees

  • Verified guest reviews

    Over 1,240 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Olean vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Olean rentals

  • 4.8 Average rating

    Olean stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated family-friendly rentals in Olean

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Superhost
Guesthouse in Olean
4.86 out of 5 average rating, 200 reviews

Cozy Country Get Away Suite

If you're passing through town on your travels or a local looking for a private get away, this is the perfect place to kick back, relax and enjoy some peace and quiet. You can sit by the fire, look across to see fireflies in the field or tilt your head back to have an amazing star-gazing experience. A one of a kind property to make memories with friends, family, or for a special romantic get away. Access to 93 acres with trails to walk or mountain bike on, fields to wander through and wildlife.

KitchenIndoor spacesParks

Top guest favorite
A cabin is nestled among tall pine trees, showcasing a rustic wooden exterior and a welcoming porch. The surrounding landscape reveals vibrant autumn foliage in hues of orange and red, creating a serene and secluded atmosphere.
Cabin in Ellicottville
4.96 out of 5 average rating, 184 reviews

Stylish & Secluded Hideaway, 5 mins to EVL

This private space is quietly tucked away in a stand of pines in the woods alongside Bryant Hill Creek. A wall of windows brings nature and natural light pouring into the space, and a fully-equipped kitchen and European bathroom provide modern comfort. Less than 4 miles outside of E-ville, it comfortably sleeps 2 adults and offers a chic and romantic setting for a couple to hide away with easy access to downtown. 4x4 a must in the snow, or simply park at the foot of the driveway. Tv & wifi.

Indoor spacesKitchenHeating

Guest favorite
Tiny home in Machias
4.86 out of 5 average rating, 459 reviews

Lucky Day Cabin Ellicottville/Ashford 30 acres

Family built cabin on 30 acre country estate, just outside exciting year round resort village of Ellicottville. Perfect for nature lovers and outdoor enthusiasts, the cabin has all necessities, similar to a tiny house. Nestled near the gardens, and surrounded by quiet rolling hills. Enjoy with door step delivered breakfast, or book a guided hike with estate owner and learn about medicinal plants and flowers, the topography of the land and a farm fresh picnic lunch on the peninsula of our lake.

KitchenIndoor spacesPets

Top guest favorite
A spacious living area is highlighted by green walls and natural light filtering through two windows. A stone fireplace serves as a focal point, with a television mounted above. Comfortable seating includes a dark sectional sofa and a leather armchair. A wooden coffee table occupies the center.
Loft in Olean
4.96 out of 5 average rating, 165 reviews

Joe's Cozy Loft

Joe's Cozy Loft is now under new management! Expect the same great accommodations and amenities as before but with seamless and Superhost service. Your stay with us includes wifi, off street parking after business hrs, a luxurious 2 person jet tub, laundry capabilities, a private deck with grill and more. We are a short walk or drive to many local restaurants and taverns. We are nestled in the heart of the the Enchanted Mountains with easy access to Ellicottville skiing, Buffalo and much more!

FamilyKitchenHiking

Top guest favorite
A spacious living area features a comfortable couch and armchair arranged around a coffee table. A stone fireplace anchors one wall, while a dining table is positioned nearby. The kitchen area, visible in the background, is equipped with modern appliances and wooden cabinetry.
Cottage in Great Valley
4.95 out of 5 average rating, 176 reviews

Country get away

Beautiful private country setting. Perfect spot to take in the fall foliage and count the stars as you sit around the fire. Newly remodeled cozy country cottage . Full kitchen and washer and dryer available . Perfect get away from the hustle and bustle of the city . Central location to all of the area attractions like Holiday Valley ski resort , Ellicottville shopping and restaurants and Seneca Allegany casino. WiFi and dish network provided in a clean and sanitized space. Gas grill available

KitchenFamilyCleanliness

Top guest favorite
A spacious living area is highlighted by a large brown leather sectional sofa adorned with decorative pillows. A vintage wooden trunk serves as a coffee table, topped with a lantern, a decorative orb, and a small plant. Soft light filters through sheer curtains.
Home in Allegany
4.96 out of 5 average rating, 182 reviews

Stylish 3-bedroom home near Ellicottville, NY

Stylish, entire residential 3 bedroom/ 1 bath home. Close to Ellicottville/skiing -30 mins., St. Bonaventure University, Cutco, Rock City Park, Allegany State Park, kayak launch, biking, and walking trail. Niagara Falls is a 1.5-hour drive, Zippo 30 minutes. Walmart and movie theater are 2 miles away. Many restaurants are nearby. A seasonal 2 screen drive-in movie theater-20 min. drive. 2 queen beds , 1 double bed, and a chair converts to a twin size bed. Fully equipped kitchen.

Indoor spacesKitchenAmenities

Guest favorite
A covered deck is seen with a wooden railing, featuring a white bench and a dark door. The yard stretches beyond, highlighted by grass and surrounding trees, while sunlight filters in, creating a bright and open atmosphere.
Apartment in Olean
4.96 out of 5 average rating, 113 reviews

Henley Hideaway

Centrally located to downtown Olean, this 2 bedroom unit is sure to make you feel at home! Enjoy easy access to local restaurants, Four Mile Brewery, and the Allegheny River Trail for a bike ride or scenic walk. Includes free Wi-Fi, off-street parking, a fenced in yard, on site laundry, a full kitchen and more. Close to St. Bonaventure University, 30 min drive to Ellicottville & Holiday Valley. This is the back unit and will share a driveway with any guests staying in the front unit

Indoor spacesKitchenWalkability

Top guest favorite
The exterior of a modern chalet is shown, featuring a striking wooden facade with large triangular windows. Surrounded by lush greenery, the building is complemented by a stone walkway and simple outdoor seating, creating a peaceful entryway to the inviting natural surroundings.
Chalet in Ellicottville
4.97 out of 5 average rating, 271 reviews

Firefly Chalet

Ideal private chalet getaway in Ellicottville NY. The property is located at the top of a hill on a private drive, giving you a beautiful overlook of the valley. The location is a 5 min drive to downtown Ellicottville and 3min drive to Holiday Valley. There are many state land hiking trails off of the private drive. Convenient location for families looking to ski for the weekend, hike locally/at Allegany State Park, and visit the beautiful town of Ellicottville NY.

Indoor spacesKitchenBiking

Guest favorite
Camper/RV in Machias
4.91 out of 5 average rating, 106 reviews

The Buzzy Bee

Escape to the Buzzy Bee, a charming vintage camper nestled in the heart of our 50-acre farm. Wake up to breathtaking sunrises, enjoy peaceful sunsets over the pastures and watch horses, donkeys, cows, ducks and other farm animals just steps away. Sleeping up to 6 guests with 4 beds. The Bee is perfect for families, coupes or friends seeking a unique farm stay experience. End your day stargazing by the campfire and enjoying the quiet beauty of country life.

KitchenFamilySleep quality

Top guest favorite
A charming cabin with a wooden exterior is set against a green lawn. The structure features multiple windows, allowing natural light to enter. A small staircase leads to the entrance, while a fenced yard surrounds the property, offering a sense of privacy and space.
Barn in Cuba
4.98 out of 5 average rating, 227 reviews

Stylish & Inviting, Close to lake, 1BR-Sleeps 2

This unique place has a style all its own. This 1BR space "delivers" when it comes to comfort and convenience. Comes with a fully equipped kitchen and all the amenities to make your stay as comfortable and easy as possible. Has a deck if you would like to just relax or enjoy a meal. This cozy space is on the second story so if you have a hard time with stairs sadly we aren't the place for you. Try us out, you won't be disappointed!!

Indoor spacesKitchenAmenities

Top guest favorite
A small log cabin is presented featuring an inviting front porch with a railing. Solar panels are visible on the roof. The surrounding area includes greenery and a gravel pathway, contributing to the rural setting.
Cabin in Great Valley
4.91 out of 5 average rating, 341 reviews

The Porcupine, featuring fiber optic internet

* Get Away From it all The Porcupine is a small, comfortable and private log cabin. And and we are proud to be solar powered! Great for a couple or a family with small children. Rural setting great for hikes or bikes. 3 miles to the village of Ellicottville. 8 miles to the Seneca Allegany Casino. And 2 miles to the slopes of Holiday Valley

KitchenIndoor spacesView

Top guest favorite
A wooden deck is presented, surrounded by towering trees and lush greenery. A small table with two folding chairs is visible, offering a tranquil spot to enjoy nature. Sunlight filters through the leaves, creating a serene outdoor setting.
Guest suite in Great Valley
4.92 out of 5 average rating, 438 reviews

Comfy studio nestled in the woods (New Listing)

Nestled in the forest only seven minutes’ drive from Holiday Valley, this contemporary style self-contained studio apartment is the perfect weekend getaway for skiing and nature-loving couples. With every luxury and convenience, you can home cook meals or barbecue on the deck overlooking the creek, with nothing but forest beyond. Relax and watch a movie on our LCD screen or use high speed internet on cable.

Indoor spacesKitchenBiking

Popular amenities for Olean family-friendly rentals

When is the best time to visit Olean?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 518ﺩ.ﺇ 470ﺩ.ﺇ 547ﺩ.ﺇ 533ﺩ.ﺇ 492ﺩ.ﺇ 551ﺩ.ﺇ 566ﺩ.ﺇ 540ﺩ.ﺇ 514ﺩ.ﺇ 533ﺩ.ﺇ 551ﺩ.ﺇ 466
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